


Servant of Hell

by GayBaeShipping



Category: Cuphead (Video Game)
Genre: Anal Fingering, Anal Sex, Blow Jobs, Drug Use, First Time Blow Jobs, Gentle Kissing, Gentle Sex, M/M, Nipple Licking, Praise Kink, Pre-Relationship, Sex Slave, Sex Trade kind of, Slow Build, Slow Romance, Very Minor, cuphead is 21+ in all my writings, implied/referenced PTSD
Language: English
Status: Completed
Published: 2020-04-27
Updated: 2020-04-27
Packaged: 2021-03-01 20:34:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,618
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23783218
Author URL: https://archiveofourown.org/users/GayBaeShipping/pseuds/GayBaeShipping
Summary: Request: (gentleness; slow build; praise kink).Instead of having them collect contracts, the Devil basically makes Cuphead a sex slave, since, you know, he was the one to make the bet, holding Mugman as collateral if he refuses. Now, since Cuphead has never had sex before, and Elder Kettle never bothered to teach the boys about the birds and the bees, he's understandably terrified. King Dice, in a moment of humanity, takes pity on Cuphead and offers to have him sleep with him instead, knowing the Devil or the other patrons would not nearly be as merciful.
Relationships: Cuphead & King Dice (Cuphead), Cuphead/King Dice (Cuphead)
Comments: 6
Kudos: 40





	Servant of Hell

**Author's Note:**

> THIS IDEA IS NOT MINE! IT WAS REQUESTED BY hattafan2593 ON A DIFFERENT WORK AND THEY GAVE ME PERMISSION TO WRITE ABOUT IT...since I thought it was an awesome idea.
> 
> May become multi-chaptered at some point, but don't hold your breath. If you do want more chapters, leave a comment saying so.
> 
> Please go and check out hattafan2593 and their work, as I think they're really good at writing. Thanks so much.

Looking back, he knew he shouldn't have done it. It seemed way too easy. A flick of a wrist, sending the dice flying across the table, and he would earn riches beyond his wildest dreams? No way was anything that easy. But, then again, Mugman always told him he was naive, and a little gullible. To be fair though, he _was_ on a winning streak. The sleazy, slightly charming manager with a dice for a head said so himself. But, he never expected _the Devil_ to show up.

So, it was a 'minor' surprise when he did. "One more roll," the Devil said, holding out red dice in his palm. "If you win, everything in this casino is yours. But, if you lose...well, everyone around here will get some fun. Deal?"

Yes, he admitted he should've thought it through first. There was no way the Devil's kind of 'fun' was playing board games and Blackjack (which he honestly thought it was). I mean, that stuff probably bored him decades ago, right? But, he didn't think twice about it.

Mugman certainly did. "Hey, Cups," he whispered, tugging his brother's shirt sleeve. "Think about this! You're risking a lot here. And for what? More weight in your pocket?"

"Come on, Mug," Cuphead nudged his brother playfully. "Imagine all the money we could have! We wouldn't be in debt our whole lives!" He grinned madly, his eyes wide and excited.

Mugman's eyes held little joy, however. It instead contained fear and desperation. "Please don't," he begged. Usually the begging style worked for Cuphead. But not today. He turned, shuffled the dice in his hands for good luck, and threw them. Everything seemed to slow down. Time and space became suddenly smaller, as he watched the dice bounce in slow-motion across the board. Since he saw everything in slow motion, he watched them flip over to the 'one' side bounce for one moment, as if wondering whether to roll once more or not, before settling down, 'ones' looking up at him mockingly.

A tall, dark shadow loomed over them. "You lost," the Devil's booming voice said, mocking. "Now you belong to me!"

Cuphead sank to his knees, in too much shock to speak. He'd lost. It seemed too hard to believe. He'd risked his brother on gold. Nothing was more valuable than Mugman. Nothing. He'd screwed up big time now. "You can have me," he said, meeting the red eyes that belonged to the dealer. "Anything you want. I don't care. Please, I'm begging you." He clasped his hands in from of him, to prove his point. "Please not Mugman."

"Cups!" Mugman cried, shocked beyond belief. 

"Anything, huh?" the Devil said, scratching his chin with a sharp claw. "Even you owe me all of you?"

"Anything," Cuphead said, swallowing his regret and pride down. "Please."

Without any hesitation, the Devil nodded. "The original plan was for you to service me and a couple of others," he said, twirling his trident between his fingers. "But, since there's one of you now, I'll have to improvise." He stood, pondering. "Oh, and one more thing." He clicked his fingers and instantly three fat demons appeared out of nowhere and grabbed Mugman. Cuphead felt his muscles slacken as if by magic, slumping forward with no control of any part of his body. "I'll be keeping him. If you decide to disobey me in any way, shape, or form, he'll pay. Got it?"

Cuphead didn't (couldn't) move for a moment. He was frozen, stuck. It was kind of relaxing, being so numb. He could stay like that forever, so limp and externally useless. He was so numb he couldn't feel any of his cheek muscles move as he slowly muttered, "Yes, sir."

He could feel the terrible teeth upturn into a smirk, and could feel his other half being dragged away....maybe forever.

\--------

King Dice wasn't stupid. He didn't have average intelligence. He could even be called savvy. He was certainly loyal. To a point. The Devil...he had never really been loyal to him in the first place. Obedient, maybe, but never loyal. He couldn't be loyal to someone who killed young children for fun. 

He had a very strict policy for not sleeping with underage girls or boys, or those that acted like it. He had never once let himself fall in love with someone like that. So when the Devil stated if they lost, they'd have fun with other lackeys, he knew exactly what he meant. They'd probably be raped, beaten whilst they were at it. It surprised him even more when the red cup took his brothers place. He clearly had no clue how rough and vulgar these patrons would be to someone so innocent. Not to mention the Devil attracted lusty people with thousands of kinks and fetishes. A lot of these people were the cutthroat, dirty type who would more likely hurt him than give him any pleasure whatsoever. He'd be black and blue all over before the night was over.

He didn't mean to follow them to the prep room. As demons dragged his limp body away, he couldn't help but follow. Maybe he didn't want him to get raped so early on? He _was_ good-looking, in the kind of way most people liked here. Young, innocent, perfect prey. "Hey, what'll happen to him?" he asked the shorter demon, who was called Rafal if he remembered correctly.

"The boss wants to make a little auction," the squat demon said. "For one night, whoever bids the highest gets the chosen partner."

"He's still doing this?" he asked.

The Devil liked auctions for random sex partners, but he stopped doing it after he got bored. Guess he's interested again. Dice followed them to a room where a row of mirrors and clothes racks stood. Some petite women and dashing men waited to be dressed, made up, and (if it really was a sex auction) drugged. They probably wouldn't be drugged during the sex unless their partner wanted them to be, so they were given it now, when it would wear off before the actual bedding, but would make them sensitive during the auctions.

If he remembered right, when they were drugged, they showed off their 'best' side, being their face when pleasured, and with the men, the bulge in their pants. He also remembered the guys with smaller bulges and women with big breasts got picked more often, though he couldn't understand why. He watched the two demons carry Cuphead to a chair, where he simply slumped uselessly.

A stab of pity hit him, and he gently lifted him into a more comfortable position. It was magic, the kind of magic that would wear off. He had to be patient. "Now that you're here, why don't you do his makeup?" Rafal asked, pulling out measuring tape to measure his sizes. Knowing the demon's quick, able fingers, it would be done in five minutes. The cup would be wearing it tonight, at least.

Dice shrugged, and lifted his chin with his finger. Their eyes met, and he was so depressed, so sad, so hurt, he felt bad. "I won't hurt you," he said softly. He said nothing in response, mainly because he couldn't. Dice glanced around. Most of the hookers here were willing, ready to get pawed unceremoniously, and even beaten if it meant money. But some, mainly men, were slumped just like Cuphead or unconscious. It seemed the Devil had been recruiting. Poor unfortunate souls.

The first time the auctions happened, most were prostitutes, but as time went on, he struck deals, made several people give themselves up for his sick pleasures.

Dice rummaged around for eyeshadow and eyeliner, knowing the cup was slowly regaining feeling in his muscles. He turned, makeup in hand, surprised to find tears on the young man's eyes. "How old are you, kid?" he asked softly.

"22," Cuphead said, softly. "What'll happen to me?"

Dice didn't want to be the one to break it to him he would be raped every single night until the Devil got bored of the auctions again. "Ever had sex before?" he simply asked. He seriously hoped he had, so he'd wouldn't be losing his virginity to someone he didn't care about.

The cup tilted his head. "Um...what?" he said.

Dice blanched. "You don't know what sex is?!" he cried.

"I was never told about it," he said simply.

Dice's cheeks coloured red, as he grudgingly began to explain about sex, between the same sexes and the opposite sexes. As he continued, his face became more and more terrified, paling. "I-I....I-" he trailed off. "I can't..."

Dice couldn't help feeling bad for the little virgin. He didn't know what to say to comfort him. He wasn't physically affectionate by nature, so what happened next shocked himself as much as Cuphead. He wrapped his arms around the smaller man, awkwardly, but still comfortingly. Cuphead shakily 'hugged' back. They stayed like that for a moment, before he pulled away. "Don't worry," Dice said. "People here aren't as bad as you think." How he wished it was true.

\---------

The auction place looked the same as it had years ago. A raised podium for the 'slaves' per se, and a golden chair that wasn't really a throne for the Devil. The newest addition was a silver chair beside the gold one. "Join me, Dice," the Devil said as they entered. "You have the best view here."

Again, Dice wasn't stupid. He had known for years that the Devil wanted him. It had taken lots of care and thought to avoid it, to snag one-night stands on nights he would supposedly make a move. Sometimes he even paid people to pretend to be his lover to he would back off a little. But he followed his boss. He couldn't get his mind off the poor cup. How he shook uncontrollably as Dice gently put on makeup for him, how he was constantly on the verge of tears. How when he started to, apologizing over and over, Dice had blatantly said, "Only real men cry."

Demons and patrons began to filter in, laughing to themselves, with drinks in their hands. A butler served Dice a mojito, which he took (gratefully?). Slowly the seats began to fill, and movement in the darkness of the stage took place. When the doors slammed shut and the lights flickered on, it began.

Most people on the stage were covered by a black blanket for now, except for one woman. Dice barely paid attention to it all, until the name 'Cuphead' cropped up, and he lifted his head.

The blanket was tossed away, and Cuphead flinched against the bright lights. His cheeks were red, his eyes dark. His outfit consisted of tight leather fittings, black and way too tight. It brought out every single line and crease. A sexy leather bra fit over his perky nipples, and the same tight leather underclothes fit over his hips.

He had cream swirled in his cup-like head, with sprinkles and a Flake. His makeup was exactly how Dice had left it; a little bit of eyeshadow and eyeliner, a hint of blush, and that was it. "Now, we have a new face to this auction," the announcing devil said. "A young adult barely 22. Will follow any and all kinks and fetishes. Obedient, and above all, a virgin." The sound of excitement that swept across the audience sickened him. They treated him as if he were a toy and not a living person with feelings. "He'll satisfy any and all needs, and look at his face."

The auctioneer lifted his chin to show off an aroused, deeply red face to the audience. More sounds of excitement, mingled with lust, echoed across the audience. "Starting at $200."

Dice couldn't listen to this. He couldn't listen to ruthless demons barter money for a boy and his ass. He just couldn't. He stood, ignoring the Devil, crossing to the door.

_The shouts of "SOLD!" Dragged away by whoever bought him._

He clenched his fists.

_Being forced down, to submit to whatever anyone wanted from him._

It wasn't his business.

_Screaming, shouting, crying out for help whilst he was mercilessly pounded._

What is wrong with me, Dice thought. He whirled around, shouting, "1K!"

Mumbles erupted from the crowd. "1, 050," someone else shouted.

"2K."

"3K!"

"5K."

With grim satisfaction, he watched the rival demon sit down grumpily. "Sold to King Dice," the auctioneer said. It hadn't been his problem at all. He'd made it his problem. Now he'd have to...damn it.

\------

Cuphead woke up laying against silk sheets. His whole body ached, probably from the constant tension of his muscles. He had never felt so weird. They gave him a pill, ordered him to swallow it, and he obeyed. He wished he hadn't. Everything was thrown into perspective. The lights were too bright. His heart pounded a thousand miles a minute, everything seemed to flash into focus. He felt warm, a little sweaty, and in pain.

Around his lower region, he was in horrifying pain. It stabbed and stabbed at his crotch, over and over again. He could see he had somehow gotten bigger, and it hurt. Every little touch felt so good. He had squeezed his legs together at one point, and a flood of ecstasy shot through him.

He couldn't feel it now. Everything felt somewhat normal. "Are you awake?" someone asked. He raised his head, almost weakly. King Dice sat at the foot of the bed, jacket hanging off a clothes hook, bow tie drooping limply off his throat. He held a glass of clear liquid (what was it called again?) in his hands. "You passed out. Thirsty?"

He held out the glass, which Cuphead took, sipped, and quickly chugged down. As soon as he drank it, it all came rushing back to him. This man bought him. He could do whatever he wanted to him now, whether Cuphead liked it, wanted it or not. But Dice simply stood and trotted away, to a bookshelf, where he started sorting through some books. "Aren't you going to do anything?" Cuphead asked after a moment.

"Nah," Dice responded. "I don't really wanna sleep with someone ages younger than me."

"And you are..."

"36."

"That isn't that bad."

"I ain't sleeping with you. By the way, those drugs should have worn off by now."

"Thank God," Cuphead said, and Dice turned with a weird look on his face. It took him a moment to realise he'd hurt his feelings. "I mean, not that I wouldn't sleep with you! It's just....I'm really scared."

Dice kneeled towards him, and smashed his lips on his, shocking him. Cuphead's mouth happened to be open, so a tongue slipped in. It tasted good, it felt good. He didn't know how to kiss, he'd never kissed anyone before, so just went along with whatever Dice did. When they pulled away, a string of saliva followed before it became too thin and broke. "You aren't that bad at kissing," Dice said. "But 'not bad' ain't gonna make them go easy on you."

"What do you mean?" Cuphead asked.

"I ain't gonna be there to save your ass every night," he stated. "If you're going to get pummelled by someone else, I should at least teach you."

Cuphead didn't know, but Dice was currently thinking, _Yeah, cause that's all it is. Teaching him how to have sex when really you want it, not him_. "Okay," Cuphead said. "Thank you for saving me. Your much kinder than the others here, I'm sure."

He let Dice cup his cheeks and kiss him again, trying his best to be good at it. "Stop trying," Dice ordered. "They'll notice if you try. Relax. Do what feels right." He laid back, calm, and untensed his muscles. He moved his tongue like Dice was doing, but not too much and not too little. "Better."

The kisses became longer, more intense, and slowly Cuphead started to touch Dice, wrapping his arms around his neck. Dice's hands traveled, too, along the annoying leather and along his exposed belly. The clip for the 'bra' was at the front, and his hands fumbled along it, unhooking it and leaning down. Cuphead hadn't been expecting anything, so when he felt a warm tongue lap over his papilla. "What - " he gasped.

"You're really sensitive here, huh?" Dice said, looking up at him with darkening eyes. "Only one lick and they're so perky." Cuphead's face turned red. He couldn't help laying back, eyes closed. The warm, wet tongue moved down, trailing against his stomach straight to his covered crotch. Gentle, caressing hands undid it, and he couldn't help but glance down. 

He had gotten suddenly bigger, standing straight up. "What the hell?"

"It's capillary action," Dice explained, rubbing his thumb over the slit. "It means you're liking it. It's called an erection, but people call it boners, and getting hard more often than not." He paused for a moment, hands perched around the shaft rigidly. "Come here a sec." He patted the edge of the bed, and Cuphead shuffled forward, member bouncing with each movement. Dice smiled at him comfortingly. "There are different parts to sex. Most men like what's called a blowjob."

"What's a blowjob?" Cuphead asked, voice cracking as he felt little waves of pleasure from Dice's hands on his erect penis.

Dice blushed. "You're really cute, you know that?" he said. Cuphead's face turned so red Dice couldn't see his nose. "You like compliments, huh?" So cute. "A blowjob is when you put this in your mouth and suck on it. There's no one technique for them, so do whatever feels good." Cuphead nodded, and began to move before Dice put him in his mouth.

"What are you..." he gasped and yelped in pleasure as Dice sucked the tip, ran his tongue along the underside, bobbed his head, and twirled his tongue around the whole thing. "Feels good..." he moaned, legs shaking, despite him trying to stop them. It felt so good. The waves of pleasure, stabs of ecstasy and the want...need...for more, more, more. "I...I feel...something...wait..."

But he didn't wait, or even pause, teasing against his aching member, mouth full. So good. Dice lifted his legs a little to get better access, kissing the tip and running his tongue along the sides. "I..." he screamed in pleasure as something shot out of the tip, something white and liquid-like.

Dice licked a little, grinning. "This is cum," he said. "It's what'll come out when you feel really good. If put inside of a woman, you can make her pregnant. But, for men, they go here."

His fingers flitted over Cuphead's entrance, circling it. "But that's..."

"I know," he said softly. "If I have to get in, I've gotta use this." He looked over at his bedstand. Sitting there was a bottle of expensive-looking lube. He squeezed some on his fingers, and gently slid on in.

"Don't put your fingers in places like that!" Cuphead cried, shocked at the feeling and the fact he actually put them in. "They're dirty!"

"It's okay," Dice said. "Good boy." Cuphead blushed harder.

"K-Keep saying that," Cuphead said. Dice glanced up curiously. "I like it when you....say nice things...to me."

Dice smiled happily, and kissed him. He kissed back, overwhelmed by pleasure and something like joy. "You're so cute," he whispered. "Relax a little. Just like that. Good boy. You're so special." His fingers brushed his temples, and Cuphead leaned forward, and licked Dice's lips. Dice paused in shock, and smiled. "So brave. Good boy."

The next kiss was more passionate, heated, intense than the last few. Cuphead didn't notice a second finger slip in, or hear a belt unbuckle. He wanted him. He wanted Dice to have him. He needed him. "Can I?" Dice asked, lining his member against Cuphead's hole. Cuphead laid back, eyes closed, and nodded. 

Slowly, it went in, tip, then shaft until he was in completely in. He moaned loudly, despite how still Dice was. "I'm going to move, okay?" he said gently, and Cuphead nodded. 

Dice pulled his hips back, and flung it back towards Cuphead, and he yelped in ecstasy. Waves of pleasure hit him, clinging to his partner with all his might. Dice never hit the same spot twice, searching for something. "So deep," Cuphead whispered.

"You're squeezing me," Dice said. "Every time I pull out, you tighten around me. Feels so good."

Cuphead moaned over and over again, wanting more, feeling his member scream for release. Dice thrust and hit something that made Cuphead's eyes roll back in his head, and he let out a moan that sent Dice through the roof. "I found a good spot, huh?" he thrust into it and Cuphead gritted his teeth to quiet his moan. "Good boy."

"I feel...good..." he whispered. "Please. I wanna...."

"Me too," Dice said, lifting his legs to get a better angle. "So cute."

The more he thrust, the closer he got to his limit, clinging to him, begging for more. He couldn't focus on anything else, didn't even notice when Dice started to pump him. Building up, everything was too good to be real, too physical to be verbal. "Cum for me," Dice whispered, and it pushed him over the edge, his orgasm hot, blinding, and...the only word to describe it was wonderful. Dice came, too, filling him with a warm liquid. He felt satisfied for the first time in his life.

"So cute," Dice said, hugging him to his chest.

If he could stay there forever, he would.

**Author's Note:**

> I really enjoyed writing this a lot.  
> Since this idea was not mine, I don't mind if you don't leave kudos, but it would mean a lot if you did look at hattafan2593's work.  
> If you want me to write any kind of story, leave a request and I'll do it.  
> Thank you


End file.
